TY - JOUR
T1 - Primary Amine Catalyzed Activation of Carbonyl Compounds: A Study on Reaction Pathways and Reactive Intermediates by Mass Spectrometry
AU - Iazzetti, Antonia
AU - Mazzoccanti, G. Bencivenni G.
AU - Righi, P.
AU - Calcaterra, A.
AU - Villani, C.
AU - Ciogli, A.
PY - 2022
Y1 - 2022
N2 - The field of organocatalysis is expanding at a fast pace. Its growth is sustained by major stimuli, such as the effort toward an understanding of the mechanisms of reaction and catalytic processes in general, the elucidation of basic properties leading to stereocontrol and the search for broad applicability and scalability of the synthetic methodology. This paper reports a thorough study based on ESI-MS spectrometry of amino-organocatalyzed model reactions under different experimental conditions. Off-line reaction monitoring of mixtures containing different catalytic systems, by ESI-MSn showed the presence of several putative intermediate species, either in their protonated or sodiated forms. In addition, enantioselective chromatography of crude reactions provides the stereochemical outcome of asymmetric reactions. The bulk of the data collected offers a clue of the intricate pathways occurring in solution for the studied reactions.
AB - The field of organocatalysis is expanding at a fast pace. Its growth is sustained by major stimuli, such as the effort toward an understanding of the mechanisms of reaction and catalytic processes in general, the elucidation of basic properties leading to stereocontrol and the search for broad applicability and scalability of the synthetic methodology. This paper reports a thorough study based on ESI-MS spectrometry of amino-organocatalyzed model reactions under different experimental conditions. Off-line reaction monitoring of mixtures containing different catalytic systems, by ESI-MSn showed the presence of several putative intermediate species, either in their protonated or sodiated forms. In addition, enantioselective chromatography of crude reactions provides the stereochemical outcome of asymmetric reactions. The bulk of the data collected offers a clue of the intricate pathways occurring in solution for the studied reactions.
KW - Mass Spectrometry
KW - asymmetric aminocatalysis
KW - organocatalysis
KW - Mass Spectrometry
KW - asymmetric aminocatalysis
KW - organocatalysis
UR - http://hdl.handle.net/10807/198671
U2 - 10.1002/ejoc.202101272
DO - 10.1002/ejoc.202101272
M3 - Article
SN - 1099-0690
SP - 1
EP - 8
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
ER -